A facile electrosynthesis of N-acyl benzotriazoles from aldehydes and benzotriazole

被引：5

作者：

Feng, Jianling ^{[1
]}

Wang, Qiang ^{[2
]}

Duan, Ruomeng ^{[1
]}

Li, Huadeng ^{[1
]}

Zheng, Ke ^{[1
]}

Wang, Xiaoxia ^{[1
]}

Xie, Guanqun ^{[1
]}

机构：

[1] Dongguan Univ Technol, Guangdong Prov Engn Technol Res Ctr, Sch Environm & Civil Engn, Key Mat High Performance Copper Clad Laminate, Dongguan 523808, Peoples R China

[2] Chinese Acad Sci, Zhongshan Inst Drug Discovery, Shanghai Inst Mat Med, Zhongshan 528400, Peoples R China

来源：

TETRAHEDRON LETTERS | 2022年 / 101卷

关键词：

N -acyl benzotriazoles; Electrosynthesis; Aldehyde; One-pot; Esterification; ACYLBENZOTRIAZOLES; AMIDES; DERIVATIVES; SECONDARY;

D O I：

10.1016/j.tetlet.2022.153904

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An electrochemical synthesis of N-acylbenzotriazoles has been developed under mild conditions with good to excellent yields using aldehydes and benzotriazole as starting materials. In addition, a one-pot reaction of aldehyde, benzotriazole and phenol has been achieved affording phenolic esters in moderate yields under the combination of electricity-on/off conditions, where N-acyl benzotriazole acted as the benign acylating reagent. It is noteworthy the research provided environmental friendly syntheses in that no superstoichiometric hazardous chemical oxidants were required, corrosive/toxic reagents have been avoided and waste production has significantly been reduced. The key of the electrochemical synthesis involves the oxidation of benzotriazole-aldehyde adduct by phthalimido-N-oxy (PINO), which was generated by N-hydroxyphthalimide (NHPI) as a redox mediator. (c) 2022 Elsevier Ltd. All rights reserved.

引用

页数：4

共 34 条

[1]

Agha K.A., 2016, ABDEL AAL ARKIVOC, P150

[2] Acyloxyphosphonium versus Aminophosphonium Intermediates: Application to the Synthesis of N-Acylbenzotriazoles [J].

Duangkamol, Chuthamat ;

Wangngae, Sirilak ;

Pattarawarapan, Mookda ;

Phakhodee, Wong .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (32) :7109-7112

[3] Organocatalyzed Anodic Oxidation of Aldehydes [J].

Finney, Eric E. ;

Ogawa, Kelli A. ;

Boydston, Andrew J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (30) :12374-12377

[4] N-Acyl Benzotriazole Derivatives for the Synthesis of Dipeptides and Tripeptides and Peptide Biotinylation by Mechanochemistry [J].

Gonnet, Lori ;

Tintillier, Thibault ;

Venturini, Natacha ;

Konnert, Laure ;

Hernandez, Jean-Francois ;

Lamaty, Frederic ;

Laconde, Guillaume ;

Martinez, Jean ;

Colacino, Evelina .

ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2017, 5 (04) :2936-2941

[5] N-Heterocyclic Carbene-Mediated Microfluidic Oxidative Electrosynthesis of Amides from Aldehydes [J].

Green, Robert A. ;

Pletcher, Derek ;

Leach, Stuart G. ;

Brown, Richard C. D. .

ORGANIC LETTERS, 2016, 18 (05) :1198-1201

[6] Identification of a novel class of quinoline-oxadiazole hybrids as anti-tuberculosis agents [J].

Jain, Puneet P. ;

Degani, Mariam S. ;

Raju, Archana ;

Anantram, Aarti ;

Seervi, Madhav ;

Sathaye, Sadhana ;

Ray, Muktikanta ;

Rajan, M. G. R. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (02) :645-649

[7] Visible-Light-Induced C(sp2)-P Bond Formation by Denitrogenative Coupling of Benzotriazoles with Phosphites [J].

Jian, Yong ;

Chen, Ming ;

Huang, Binbin ;

Jia, Wei ;

Yang, Chao ;

Xia, Wujiong .

ORGANIC LETTERS, 2018, 20 (17) :5370-5374

[8] Acylbenzotriazoles as advantageous N-, C-, S-, and O-acylating agents [J].

Katritzky, AR ;

Suzuki, K ;

Wang, ZQ .

SYNLETT, 2005, (11) :1656-1665

[9] The preparation of N-acylbenzotriazoles from aldehydes [J].

Katritzky, AR ;

Vakulenko, AV ;

Jain, R .

ARKIVOC, 2003, :131-139

[10] Efficient conversion of carboxylic acids into N-acylbenzotriazoles [J].

Katritzky, AR ;

Zhang, YM ;

Singh, SK .

SYNTHESIS-STUTTGART, 2003, (18) :2795-2798

← 1 2 3 4 →